Tetrahydrofuran → HCID 86634752, compound

HRID 911025Notes

Reaction equation

HRID 911025 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[O:4][C:5]1[C:10](C=O)=[CH:9][N:8]=[C:7]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH3:19])[N:18]=2)[CH:6]=1.[CH3:25][O:26][C:27](=[O:48])[CH:28]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH2:49]1COCC1>>[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]([NH:13][C:14]2[S:15][CH:16]=[C:17]([CH3:19])[N:18]=2)[N:8]=[CH:9][C:10]=1/[CH:49]=[CH:28]/[C:27]([O:26][CH3:25])=[O:48]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester2×HCID 57898918HCID 57898918, compound

Product 1

HCID 86634752HCID 86634752, compound

Procedure

A 25 mL round-bottomed flask is charged with 4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)nicotinaldehyde (534 mg, 1.54 mmol) and THF (10 mL). Methyl(triphenylphosphoranylidene)acetate (668 mg, 2.00 mmol) is added and the reaction mixture is stirred at room temperature. After 4 hours, additional methyl(triphenylphosphoranylidene)acetate (668 mg, 2.00 mmol) is added and the reaction mixture is and stirred overnight. The precipitate is filtered, concentrated, and purified by silica gel chromatography (1:1 EtOAc in hexanes) to afford (E)-methyl 3-(4-(2,6-difluorophenoxy)-6-(4-methylthiazol-2-ylamino)pyridin-3-yl)acrylate.

Workup

  1. stirringstirred overnight
  2. filtrationThe precipitate is filtered
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (1:1 EtOAc in hexanes)

Sources & evidence

ORD record
ord-e3c161616f6341e48b91f93308480778
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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